Pyridonecarboxylic acid derivatives substituted by a bicyclic amino group as antibacterials

Abstract

This invention relates to a N.sub.1 -(halogenocyclopropyl)-substituted pyridonecarboxylic acid derivative represented by the following formula (I): ##STR1## wherein X.sup.1 is a halogen atom or a hydrogen atom; X.sup.2 is a halogen atom; R.sup.1 is a hydrogen atom, a hydroxyl group, a thiol group, a halogenomethyl group, an amino group, an alkyl group or an alkoxy group which may have a substituent group; R.sup.2 is a group represented by the following formula (II): ##STR2## wherein R.sup.3 and R.sup.4 are independently a hydrogen atom or an alkyl group and n is an integer of 1 or 2; A is a nitrogen atom or a partial structure of the following formula (III): ##STR3## wherein X.sup.3 is a hydrogen atom, a halogen atom, a cyano group, an amino group, an alkyl group, a halogenomethyl group, an alkoxyl group or a halogenomethoxyl group which may have a substituent group; and R is a hydrogen atom, a phenyl group, an acetoxymethyl group, a pivaloyloxymethyl group, an ethoxycarbonyl group, a choline group, a dimethylaminoethyl group, a 5-indanyl group, a phthalidynyl group, a 5-alkyl-2-oxo-1,3-dioxol-4-ylmethyl group, a 3-acetoxy-2-oxobutyl group, an alkyl group, an alkoxymethyl group or a phenylalkyl group, and provides a heterocyclic compound useful as antibacterial drugs.

Claims

1. An N.sub.1 -(halogenocyclopropyl)-substituted pyridonecarboxylic acid derivative represented by formula (I): ##STR52## wherein X.sup.1 represents a halogen atom or a;

X.sup.2 represents a halogen atom;

R.sup.1 represents a hydrogen atom, or an amino group;

R.sup.2 is a group represented by formula (II): ##STR53## wherein R.sup.3 and R.sup.4 represent a hydrogen atom and n is an integer of 1;

A represents a partial structure of formula (III): ##STR54## wherein X.sup.3 represents an alkyl group having 1 to 6 carbon atoms, a halogenomethyl group, an alkoxyl group having 1 to 6 carbon atoms or a halogenomethoxyl group,

R represents a hydrogen atom, a phenyl group, an acetoxymethyl group, a pivaloyloxymethyl group, an ethoxycarbonyl group, a choline group, a dimethylaminoethyl group, a 5-indanyl group, a phthalidynyl group, a 5-alkyl-2-oxo-1,3-dioxol-4-ylmethyl group, a 3-acetoxy-2-oxobutyl group, an alkyl group having 1 to 6 carbon atoms, an alkoxymethyl group having 2 to 7 carbon atoms or a phenylalkyl group composed of an alkylene group having 1 to 6 carbon atoms and a phenyl group; or a salt thereof.

2. The compound or a salt thereof according to claim 1, wherein said halogenocyclopropyl group in the formula (I) is a 1,2-cis-2-halogenocyclopropyl group.

3. The compound or a salt thereof according to claim 2, wherein R.sup.2 in the formula (I) is a stereochemically pure substituent.

4. The compound or a salt thereof according to claim 1, 2 or 3, wherein said halogenocyclopropyl group in the formula (I) is a stereochemically pure substituent.

5. The compound or a salt thereof according to claim 4, wherein said halogenocyclopropyl group is a (1R,2S)-2-halogenocyclopropyl group.

6. The compound or a salt thereof according to claim 5, wherein X.sup.2 is a fluorine atom.

7. An antibacterial composition, which comprises the compound of the formula (I) or a salt thereof as an active ingredient, together with a pharmaceutically acceptable carrier.